Family-friendly holiday rentals in Downtown Jacksonville

Luxurious Craftsman in Historic San Marco

Never Drive Again! Immaculately renovated San Marco Bungalow, just a minute from excellent restaurants, retail, entertainment, hospitals & easy transit (via San Marco's FREE Beachside Buggy App) to everything else. Features include an inviting front porch, interior foyer, charming living room w/gas fireplace, new kitchen w/SS and granite, indoor laundry, historic architectural features, and private backyard w/ sitting area, fire pit, games & BBQ! Incredible location with unmatched walkability!

Carriage House San Marco - a Hip Historic Space

Comfortable for corporate or WFH travelers, short visits & extended stays. A unique Hip Historic space, Carriage House is located within blocks to restaurants, shops, downtown Jacksonville, the sports and entertainment district, and minutes to hospitals! This is a comfy, clean, and stylish upstairs studio apartment boasting 1 bedroom plus 1 full bathroom to accommodate 3 guests (with futon). Close proximity to Jax Water Taxi. Please view our other listings at this address by opening my profile.

Better than your average Jacksonville hotel room!

Tired of taking out the trash, and stripping the bed at most Airbnbs? Our quiet and cozy suite is centrally located in the historic Springfield district, next to downtown Jacksonville. This unit is furnished with a queen bed, a queen pull-out sofa bed, and an amazing La-Z-Boy recliner perfect for naps. The bathroom is updated, with excellent water pressure. And, the front porch is exclusive for our guests. There is a stocked Keurig, as well as a refrigerator and microwave, but no kitchen.

Modern & Historic quiet house near Arenas|Yard|R&R

Historic Charm + Modern Comfort. Immaculately clean house in historic Sprinfield. Quiet neighborhood within 6 minute drive to Jacksonville arenas. Plenty street parking (SP) infront of the Property. No additional pet fees. A large fenced yard. House is within walking distance of restaurants and breweries. Fully equipped for a great stay. The house was designed to resemble a century-old historic home. Features front and back porches with a built-in L bench for family and friends to gather.

The 1910 General Store - residence

This historic country general store, listed on the National Register of Historic Places, is within easy walking distance to art galleries and cultural events, restaurants, bars, night life, and family-friendly activities. This residence is good for couples, solo adventurers, business travelers, families, and furry friends (pets, max. of 2). We are unable to allow guests to host gatherings and house parties. Off street parking available. "Historic hospitality with a southern accent!"

Modern Riverside Private Studio

Enjoy a stylish experience at this brand new renovated suite in the heart of Riverside. You will find everything you need in our cozy and private studio. The space includes small kitchen with mini fridge, microwave, toaster, and coffee maker. Within walking distance to many restaurants, breweries, coffee shops and the best bike rental shop in town. We are centrally located to walk to Historic Five Points, King Street, or the St John’s waterfront and a short drive to San Marco & Downtown.

*Historic Dream *Walkable *1 mile to Downtown Jax

The Lilly House sleeps 6 and offers gated parking, a covered cozy porch with a swing, and courtyard featuring a fire pit, grill, and yard games. WALKING DISTANCE to restaurants, breweries, and coffee shops. Enjoy a stocked kitchen, on-site laundry, smart TVs, WiFi, Bluetooth radio, record player, and workspace. Just 1 mile from downtown Jacksonville and minutes from the TIAA Bank Stadium, Vystar Arena, and more. Pets and events allowed with prior approval. Book your stay today!

Vintage Riverside Cottage w/ King Bed

Welcome to our 1901 "doll house" with timeless charm and contemporary upgrades. From the original cast iron tub that we refinished ourselves, to the brand new butcher block kitchen. You'll find yourself in the Brooklyn area of Riverside and close to 5-points, avondale , murray hill , DT Jax and 4 miles from Daily's Place & Vystar Veterans Arena. Our home has been converted into a Duplex, with this being located in the back and a quiet office located in the front of the building.

New Luxury Riverside • Walk to Dining • Sleeps 6

Discover a newly constructed, stylish and spacious home in the heart of Riverside, Jacksonville. Perfect for families, groups, or business travelers, this modern 3-bedroom, 2-bath home offers comfort and design. Enjoy an open-concept living space, fully equipped kitchen, and bright layout. Located minutes from top restaurants, bars, and shops—everything you need is right at your doorstep. Perfect for families, groups, and wedding guests visiting Riverside

Brick Carriage House

This unique place has a style all its own. Our newly renovated 2nd story apartment almost feels like you're in a treehouse. We live next door in the Main House. Situated in the heart of Jacksonville's Historic Springfield, you'll be in walking distance to our local restaurants and breweries and just a few miles from downtown where you can walk long the St. John's River or check out some local Museums. Also, it's walking distance to UF Health.

Designer Loft near Downtown

Experience luxury and style in this brand new studio apartment, nestled in the heart of Historic Springfield, just moments away from downtown Jacksonville. Immerse yourself in modern elegance with high-end finishes, stainless steel appliances, and sleek concrete countertops. Discover comfort and convenience in a prime location, with easy access to the city's vibrant attractions.

The Great Gatsby - Luxury Historic Riverside

The perfect downtown haven to relax and refresh after an enjoyable night out on the town. Enjoy attractions just minutes away and come back to the brand new fully renovated apartment unit to rest and get rejuvenated for the next day. Slow down for a bit in our one-bedroom, which is perfect for staycations, work-cations, and, of course, vacations.